Downtown street view of Annapolis, Maryland. Image credit grandbrothers via Shutterstock

8 Must-See Historic Towns in Maryland

Maryland is a Mid-Atlantic state comprising many waterways and a coastline that borders the Chesapeake Bay and Atlantic Ocean. The most populous city is Baltimore, which has long been a major seaport. Maryland is historically significant, having been one of the original 13 colonies and being the birthplace of the Star Spangled Banner.

This article focuses on the abundant history of Maryland by describing eight must-see historic towns of the state.


The people and traffic in the main street of Annapolis, Maryland
The people and traffic in the main street of Annapolis, Maryland, via Wirestock Creators /

Annapolis is Maryland's capital and is notable for being the home of the US Naval Academy on the Chesapeake Bay. The historic district is filled with 18th-century brick houses, including the domed Maryland State House from the 1700s. The Hammond-Harwood House is another historical landmark and today serves as a museum for a unique look into Annaplolis' past.

Annapolis, Maryland, USA from Annapolis Harbor at dusk
Annapolis, Maryland, USA from Annapolis Harbor at dusk

The waterfront historic district has changed little in 300 years; the original buildings are now stores, pubs, and restaurants. Start on Main Street for a leisurely walking tour through the district. This will lead you down the hill to the City Dock overlooking the harbor. If you head toward West Street, you enter the Art District with art galleries and modern restaurants. Annapolis is one of the most historic towns in the area, and it requires at least a couple of days to discover what it has to offer fully.

St. Mary's City

Historic Saint Marys City.
Historic Saint Marys City.

St. Mary's City, Maryland, stands as a beacon of historical significance amidst the modern landscape. Unlike other Maryland towns, its allure lies in its rich tapestry of colonial heritage. As the site of Maryland's first capital, St. Mary's City boasts landmarks that chronicle America's earliest beginnings.

The Historic St. Mary's City Museum offers a glimpse into colonial life, while the Maryland Dove, a meticulously crafted replica ship, evokes the era's maritime prowess. St. Mary's College of Maryland, nestled within the city, fosters academic inquiry amid historic surroundings. Moreover, the St. Mary's River State Park provides a serene retreat, connecting visitors to nature.

Amidst this historical backdrop, quaint commercial spots like the Waterfront Café add a modern touch, blending contemporary comforts with centuries-old charm. St. Mary's City invites exploration, offering a journey through time unmatched by any other Maryland town.

St. Michaels

Downtown St. Michaels, Maryland
Downtown St. Michaels, Maryland. Image credit MeanderingMoments via

Sitting on Maryland's Chesapeake Bay, St. Michaels provides a timeless feel and showcases the historical significance of the East Coast. Its gorgeous waterfront, lined with colonial-era homes and docks holding sailboats, invites visitors to step back in time. St.

As mentioned, St. Michaels has a rich maritime heritage, evident in landmarks like the Chesapeake Bay Maritime Museum, which preserves the region's seafaring legacy. The town's iconic lighthouse, Hooper Strait Lighthouse, stands as a beacon of its maritime past, offering panoramic views of the bay. Additionally, the Old Brick House and Christ Episcopal Church, both dating back to the 18th century, highlight St. Michaels' colonial roots.

Historical treasures, boutique shops, and local restaurants thrive here, adding modern flair to the town's storied ambiance. St. Michaels' fusion of historical landmarks and commercial offerings creates an unparalleled destination for history enthusiasts and leisure seekers alike.


Street sign in downtown Frederick, Maryland
Street sign in downtown Frederick, Maryland, via George Sheldon /

Frederick, known for its well-preserved historic district, captivates visitors with its architectural splendor and cultural significance. Founded in 1745, the town boasts landmarks such as the Schifferstadt Architectural Museum, an exceptional example of colonial German architecture. The National Museum of Civil War Medicine sheds light on the medical practices of the era, offering a poignant perspective on the impact of conflict on society.

Drone shot of Carroll Creek Linear Park in Frederick, Maryland.
Drone shot of Carroll Creek Linear Park in Frederick, Maryland.

Commercially, downtown Frederick thrives with eclectic shops, art galleries, and culinary delights of all kinds, housed within 18th and 19th-century buildings, creating a harmonious blend of past and present. You are sure to learn something about this town's early history whether you are actively looking for it or simply sitting down with a cup of coffee on its historic streets.


The charming business district in Chestertown, Maryland.
The charming business district in Chestertown, Maryland.

Chestertown is yet another cool location on this list that is abundant in colonial history. It is visually striking with its tree-lined streets and historic waterfront.

Established in 1706, it played a pivotal role in the American Revolution and boasts landmarks such as the Chestertown Historic District, renowned for its well-preserved Georgian and Federal-style architecture. The Geddes-Piper House Museum offers insights into the town's colonial past, showcasing period furnishings and artifacts. Along High Street, visitors can explore local boutiques, art galleries, and restaurants housed among, or even with, several well-preserved historic structures, immersing themselves in the town's exciting and bustling commercial scene while appreciating its architectural heritage.

Be sure to try some locally caught crabs, a delicacy to the area, for lunch or dinner on your visit.

Havre de Grace

An empty street in Havre De Grace city at dusk.
An empty street in Havre De Grace city at dusk. Image credit Wirestock Creators via Shutterstock.

Havre de Grace, situated at the mouth of the Susquehanna River, holds a unique position in Maryland's history and landscape. Established in 1785, its strategic location led to its development as a bustling port town.

The Concord Point Lighthouse, dating back to 1827, stands as the oldest continuously operated lighthouse in Maryland and offers panoramic views of the Chesapeake Bay. The Havre de Grace Decoy Museum pays homage to the town's rich tradition of decoy carving and waterfowl hunting. Commercially, the town's Main Street buzzes with activity, featuring antique shops, art studios, and waterfront dining establishments, all contributing to its ambiance and historical allure.

The origin of the French-sounding name, Havre de Grace, is based after the French port town of the same name across the ocean.


Cambridge, Maryland Lighthouse and marina.
Cambridge, Maryland Lighthouse and marina.

The town of Cambridge, sitting along the shores of the Choptank River, contains a vast and interesting history dating back to 1684. Check out the many destinations that illuminate the stories past of this area of Maryland.

The Richardson Maritime Museum offers a glimpse into the town's seafaring past, with exhibits on boatbuilding and the seafood industry. The Harriet Tubman Museum and Educational Center honors the legacy of the famed abolitionist who was born nearby. Historic High Street, lined with Victorian-era buildings, showcases the town's architectural heritage and hosts various shops and eateries.

Cambridge's history is further enriched by the 19th-century Dorchester County Courthouse, which witnessed significant events during the Civil War. Today, visitors can explore this vibrant town, learn about its storied past, and enjoy scenic views along the riverfront promenade.


The historic district of Berlin, Maryland.
The historic district of Berlin, Maryland.

Berlin, known as "America's Coolest Small Town," charms all visitors and residents with its well-preserved historic district and expansive scene for budding artists.

Founded in 1868, the town boasts architectural treasures such as the Calvin B. Taylor House Museum, showcasing Victorian-era furnishings and artifacts. The Atlantic Hotel, a landmark since 1895, stands as a testament to the town's hospitality. Main Street, adorned with colorful storefronts and flower-filled planters, invites visitors to explore unique local stores, art galleries, and cozy cafes.

Berlin's annual events, including the Berlin Jazz & Blues Bash and Oktoberfest, celebrate its cultural heritage and community spirit. With its picturesque streets and welcoming atmosphere, Berlin provides you with a delightful blend of history, culture, and small-town vibes on Maryland's Eastern Shore.

Learn More about Maryland Today!

Maryland with its strong historical roots in major events such as the European settlement of America, the revolution for American independence, and the Civil War, and beyond, is a haven for history buffs from all around the world. A pleasant climate, various cultural landmarks and restaurants serving fresh local foods, and a huge variety of natural parks, also add to any trip one may take in the coastal state. Hopefully, this list is just the start of your next road trip!

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